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This assumes that the user plans to go online using these OSs. For offline use (legacy/classic gaming, or embedded tasks) there'd be no problem.

> Both are really good plans if you want to get 0wned.

It is wise to point that out; running an old OS on old equipment or in a VM is perfectly viable, but one should NEVER connect those machines to the open Internet.

2019 malware likely won't run on Windows 95. The kind of malware you'd stumble across in your normal online activity will mostly target Windows 10 and back to XP, and will be written to that environment and its APIs. Given the need to minimise size and detectable features.

Naturally I would not rely on this for my own online safety. A motivated adversary with a specific target in mind would no doubt learn that a vintage Windows 95 install was present, or maybe just throw everything at it.